(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester

Base Information

• Chemical Name: (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester
• CAS No.: 160204-82-0
• Molecular Formula: C₂₉H₄₂FNO₆SSi
• Molecular Weight: 579.805
• Mol file: 160204-82-0.mol

Synonyms:(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester

Chemical Property of (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester

There total 15 articles about (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

trifluoromethylsulfonic anhydride (358-23-6) + (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester (205647-15-0) → (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester (160204-82-0)

Guidance literature:

(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

trifluoromethylsulfonic anhydride; In tetrahydrofuran; at -78 - 0 ℃; for 6h;

DOI:10.1021/jo9722156

Reference yield: 41.0%

4-(4-Fluorophenyl)-3-formyl-2-isopropyl-5-methyl-1-methylsulfonylpyrrole (139993-90-1) + methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate (147118-35-2) → (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester (160204-82-0)

Guidance literature:

In acetonitrile; for 24h; Heating;

DOI:10.1021/jo00104a049

Reference yield:

(S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester (109721-08-6) → (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester (160204-82-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -30 - 2 °C

1.2: 100 percent / tetrahydrofuran; hexane / 0.92 h / -66 - -30 °C

2.1: 74 percent / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 0.92 h / 0 - 15 °C

3.1: 98 percent / methanol / 0.53 h / 0 °C

4.1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 0 °C

4.2: 1.98 g / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / 0 °C

5.1: 91 percent / toluene / 1 h / Heating

6.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

6.2: 62 percent / tetrahydrofuran / 6 h / -78 - 0 °C

With n-butyllithium; potassium tert-butylate; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; tert-butyl alcohol; 1.1: Metallation / 1.2: Acylation / 2.1: Cyclization / 3.1: Ring cleavage / 4.1: Metallation / 4.2: Condensation / 5.1: Elimination / 6.1: Metallation / 6.2: mesylation;

DOI:10.1021/jo9722156

upstream raw materials:

4-(4-Fluorophenyl)-3-formyl-2-isopropyl-5-methyl-1-methylsulfonylpyrrole

methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate

trifluoromethylsulfonic anhydride

(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester

Downstream raw materials:

(E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester

(3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester